The proposed work of this project is the synthesis of conformationally eclipsed rigid analogs of ephedrine. The compounds to be prepared are cis and trans 2-methyl-3-phenylazetidin-3ol and cis and trans 2-phenyl-2-hydroxycyclobutylamine. These compounds will be separated into their enantiomeric forms and the use of optical rotatory dispersion and circular dichroism as a method of configuration assignment will be investigated. Once the compounds are obtained pharmacological studies on isolated adrenergically inervated tissues will be carried out. These studies of ephedrine analogs should give a better insight as to the absolute structural requirements of adrenergic agents for interaction with neuroeffector and/or uptake and metabolic sites. This knowledge should lead to a much better understanding of adrenergic drugs and their mechanism of action at the molecular level. Bibliographic references: R. R. Ruffolo, Jr., D. D. Miller and P. N. Patil, Biochemical and Pharmacological Correlates for the Effects of L(plus)-Isomers and Beta-Desoxy-Sympathomimetic Amines, Fed. Proc., 34, 794 (1975); Duane D. Miller, Fu-Lian Hsu, Michael Miasnik, and Popat N. Patil, Stereochemical studies of Adrenergic Drugs, 7th Central Regional Meeting, ACS, Abstract MEDI-63 (1975).